EP0680751B1 - Lipid vesicles containing compositions - Google Patents

Lipid vesicles containing compositions Download PDF

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Publication number
EP0680751B1
EP0680751B1 EP95400967A EP95400967A EP0680751B1 EP 0680751 B1 EP0680751 B1 EP 0680751B1 EP 95400967 A EP95400967 A EP 95400967A EP 95400967 A EP95400967 A EP 95400967A EP 0680751 B1 EP0680751 B1 EP 0680751B1
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European Patent Office
Prior art keywords
emulsion
paste
aqueous phase
proteins
phase
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EP95400967A
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German (de)
French (fr)
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EP0680751B2 (en
EP0680751A1 (en
Inventor
Robert Voultoury
Philippe Flavigny
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Laboratoires de Biologie Vegetale Yves Rocher SA
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Laboratoires de Biologie Vegetale Yves Rocher SA
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0053—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J1/00—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites
    • A23J1/14—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites from leguminous or other vegetable seeds; from press-cake or oil-bearing seeds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/14—Liposomes; Vesicles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A61K8/553—Phospholipids, e.g. lecithin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/645—Proteins of vegetable origin; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations

Definitions

  • the present invention relates to compositions comprising lipid vesicles and aqueous emulsions containing these vesicles and a process for their manufacture.
  • the present invention relates more specifically to compositions comprising lipid vesicles which comprise as envelops the proteins and phospholipids present in the seeds oilseed.
  • the oil (mainly triglycerides) was present under the form of oily body with an average diameter of 1 to 10 micrometers comprising a central oil core surrounded by an envelope proteins (oleosins) and phospholipids (J. Tzen et al., J. Cell Bio, 117, 327, 1992).
  • J. Raymond et al. (Perfumes, cosmetics, aromas, vol. 56, May 1984) described the separation of a protein isolate from from sunflower meal for use in cosmetology.
  • compositions cosmetics containing an extract of sunflower meal comprising mainly polyphenols.
  • proteins constituting the envelope of oily bodies are of two types: certain proteins do not are not glycosylated and other proteins are glycosylated.
  • the object of the present invention is to provide compositions comprising lipid vesicles which comprise all the proteins and phospholipids present in the envelope oily bodies and therefore which include both proteins not glycosylated and glycosylated proteins identical to those present in the envelope of oily bodies.
  • oilcakes are recovered which contain still a significant fraction of proteins and phospholipids present in the envelope of oily bodies. These cakes contain in addition to a rate of unextracted oil which can represent from 10 to 30% in weight.
  • the present invention more specifically aims to provide compositions comprising new lipid vesicles and emulsions containing them, enhancing oilseed meals.
  • the present invention relates to cosmetic, therapeutic or food compositions
  • lipid vesicles having an average size of 0.1 to 20 micrometers, in particular 1 to 8 micrometers, and comprising an envelope made up practically all of the proteins and phospholipids present in the oily bodies of oil seeds, surrounding a nucleus comprising at least exogenous lipids and / or lipophilic substances exogenous.
  • the invention also relates to such compositions comprising an aqueous emulsion comprising lipid vesicles dispersed in an aqueous phase.
  • the expression "practically all the proteins and phospholipids present in the body oily oilseeds” means that found in the envelope of the vesicles practically the same constituents as in the envelope of oily bodies and that proteins include both non-glycosylated proteins and glycosylated proteins.
  • proteins and phospholipids found in oilseeds are those present in oilseed meals.
  • oilseed meals we can cite soybean meal, pistachio, macadamia, sunflower, rapeseed, peanut, almond, hazelnut, sesame, borage, wheat germ, jojoba.
  • oil cakes obtained from seeds with a high oil content (pistachio, macadamia, peanut, jojoba, hazelnut, almond).
  • the grinding of oil cakes can be carried out by conventional mills, such as knife mills, advantageously until a particle size of less than 0.1 mm is obtained.
  • Ground cake may be subject irradiation for debacterization up to an intensity of 10 kgray and kept under inert atmosphere in hermetically sealed packaging.
  • exogenous lipids is meant the supply lipids, that is to say which are added and which are not present in the oil cakes crushed.
  • These lipids which are added to the ground cakes can be lipids of the same type as those present in the oilseed used (lipids endogenous) or other lipids.
  • lipids endogenous lipids endogenous
  • lipophilic substances can be added such as vitamins (vitamins D, A, E, K), sunscreens (such as Parsol MCX and Parsol 1789 from Givaudan or benzophenone-3), complex lipophilic mixtures (Titan M262CD from Kemira Oy) added possibly mineral oil, carotene, silicone (e.g. DC 200 from Dow Corning), fatty esters.
  • Lipid vesicles can contain from 0.01% to 100% by weight of exogenous lipids or exogenous lipophilic substances.
  • the aqueous phase is then added, advantageously at room temperature and under an inert atmosphere (vacuum or nitrogen).
  • This aqueous phase can comprise, in addition to water, various hydrophilic constituents.
  • the addition of the aqueous phase is generally carried out so as to have a paste / aqueous phase weight ratio of about 40/60 at 5/95. We prefer a ratio 30/70 to 5/95.
  • the whole is subjected to a agitation which can be significant, for example using a grinder colloidal.
  • the emulsion obtained is then optionally subjected to a decantation and / or filtration, for example on a sieve of 200 micrometers.
  • the emulsion obtained is relatively diluted and in general it it is necessary to concentrate this emulsion by centrifugation. To this end, you can use a plate centrifuge adapted to the phase rate lipid.
  • the product obtained is a concentrate of lipid particles, the level of lipophilic components can vary from approximately 20 to 70% by weight according to the manufacturing conditions.
  • the lipid suspension Before or after this centrifugation, the lipid suspension can undergo a heat treatment, the conditions of which can vary from 2 seconds to 10 minutes for temperatures from 80 ° C. to 140 ° C. An operation can then be carried out, if desired. homogenization using a Gaulin type device for example, which operation may have pressure conditions varying from 5 to 400.10 5 Pa.
  • This concentrate of lipid particles can be taken up and diluted with an aqueous phase of the type described below.
  • This phase aqueous can be thickened using gelling agents such as xanthan gum, sclerane gum, bentone and derivatives, cellulose and derivatives, carbopol and derivatives, carob, carrageenans and derivatives, present at concentrations from 0 to 2% by weight.
  • the concentrate of lipid particles can also be churned using dairy techniques to obtain a butter that is compresses to express the water.
  • the emulsions thus obtained generally have sizes particle sizes from 0.1 to 20 micrometers.
  • compositions comprising lipid vesicles according to the invention (for example compositions moisturizers, sun protection compositions, compositions nourishing).
  • compositions of an emulsifying system natural leads to better tolerance the final product.
  • the emulsions according to the invention also find applications in the field of food products.
  • the present invention therefore also relates to food compositions comprising lipid vesicles according to the invention.
  • lipid vesicles As an example we can cite vitamin supplements without cholesterol, fermented milk desserts, yogurts and whipped creams. Fermented milk desserts and yogurts can be made by adding lactobacillus strains to an emulsion according to the invention and then incubating for 5 hours at approximately 35 ° C. Whipped creams can be obtained by adding 90 parts of a propellant (CO 2 or N 2 O) to 10 parts of a concentrated emulsion according to the invention, supplemented with the usual food additives (flavors and sugars).
  • a propellant CO 2 or N 2 O
  • the emulsions according to the invention also find pharmaceutical applications for use human or veterinary, in connection with the intrinsic qualities of oleosins (small size and lipophilicity).
  • the present invention thus also relates to pharmaceutical compositions.
  • the emulsions obtained include proteins that are very similar to mammalian apolipoproteins; in other words, it is believed that lipases mammals recognize the proteins of the emulsions according to the invention, which allows the attachment of lipases on the membranes of the particles and consequently the degradation of the lipid substrates of the lipases concerned.
  • the meal contains approximately 20% by weight of triglycerides.
  • Example 1 We operate as in Example 1 with a meal of macadamia (containing 25% by weight of triglycerides), adding to 30 parts by weight of meal, 70 parts by weight of triglycerides ( macadamia or other oilseeds).
  • Water is added to the dough at the rate of 900 parts by weight.
  • compositions will be given below obtained according to the method of the invention.
  • Example A Face milk
  • Concentrate A is produced as described in Example 1, from vegetable oil.
  • Example B Total sunscreen milk
  • Concentrate C is produced as described in Example 1, from vegetable oil with added fatty esters of jojoba (5 to 10%).
  • Concentrate D is produced as described in Example 1, using oil with high gamma linolenic triglyceride content added vitamin D (500 IU / g max) or A (1500 IU / g max).
  • Example 2 We proceeded as in Example 2, starting from an oil cake of macadamia.
  • Protein purification was carried out by chromatography molecular sieving on a balanced Superose 6 column and eluted in 10 mM Tris / HCl buffer 0.07 M SDS, pH 8.2.
  • Fractions 7 and 36 are recognized by the directed serum against ⁇ -glucosidase, which is not the case for fraction 43. The recognition is therefore due to the presence of glycosidic chains in fractions 7 and 36 which do not appear for fraction 43.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biochemistry (AREA)
  • Dermatology (AREA)
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  • Dispersion Chemistry (AREA)
  • Molecular Biology (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract

New lipid vesicles have an average particle size of 0.1-20 microns and comprise a shell consisting of practically all the proteins and phospholipids present in the oil bodies of oil seeds surrounding a core comprising exogenous lipids and/or exogenous lipophilic substances. Also claimed is an aq. emulsion contg. lipid vesicles as above dispersed in an aq. phase. Also claimed is a process for preparing an aq. emulsion as above. Also claimed are cosmetic, food and therapeutic compsns. contg. lipid vesicles as above.

Description

La présente invention concerne des compositions comprenant des vésicules lipidiques et des émulsions aqueuses contenant ces vésicules et un procédé pour leur fabrication.The present invention relates to compositions comprising lipid vesicles and aqueous emulsions containing these vesicles and a process for their manufacture.

La présente invention concerne plus spécifiquement des compositions comprenant des vésicules lipidiques qui comprennent comme enveloppe les protéines et les phospholipides présents dans les graines d'oléagineux.The present invention relates more specifically to compositions comprising lipid vesicles which comprise as envelops the proteins and phospholipids present in the seeds oilseed.

On a considéré jusqu'à présent que dans les graines d'oléagineux, l'huile (triglycérides essentiellement) était présente sous la forme de corps huileux d'un diamètre moyen de 1 à 10 micromètres comprenant un noyau central d'huile entouré d'une enveloppe constituée de protéines (oléosines) et de phospholipides (J. Tzen et al., J. Cell Bio, 117, 327, 1992).So far it has been considered that in seeds oilseed, the oil (mainly triglycerides) was present under the form of oily body with an average diameter of 1 to 10 micrometers comprising a central oil core surrounded by an envelope proteins (oleosins) and phospholipids (J. Tzen et al., J. Cell Bio, 117, 327, 1992).

Par ailleurs, J. Raymond et al. (Parfums, cosmétiques, arômes, vol. 56, mai 1984) ont décrit la séparation d'un isolat protéique à partir de tourteaux de tournesol pour une utilisation en cosmétologie.Furthermore, J. Raymond et al. (Perfumes, cosmetics, aromas, vol. 56, May 1984) described the separation of a protein isolate from from sunflower meal for use in cosmetology.

De plus, WO 91/11169 a décrit des compositions cosmétiques contenant un extrait de tourteaux de tournesol comprenant essentiellement des polyphénols.In addition, WO 91/11169 described compositions cosmetics containing an extract of sunflower meal comprising mainly polyphenols.

On a maintenant découvert que les protéines constituant l'enveloppe des corps huileux sont de deux types : certaines protéines ne sont pas glycosylées et d'autres protéines sont glycosylées.We have now discovered that the proteins constituting the envelope of oily bodies are of two types: certain proteins do not are not glycosylated and other proteins are glycosylated.

La présente invention a pour but de fournir des compositions comprenant des vésicules lipidiques qui comprennent l'ensemble des protéines et des phospholipides présents dans l'enveloppe des corps huileux et donc qui comprennent à la fois des protéines non glycosylées et des protéines glycosylées identiques à celles présentes dans l'enveloppe des corps huileux.The object of the present invention is to provide compositions comprising lipid vesicles which comprise all the proteins and phospholipids present in the envelope oily bodies and therefore which include both proteins not glycosylated and glycosylated proteins identical to those present in the envelope of oily bodies.

Par ailleurs, on sait que lors de l'extraction des huiles végétales des oléagineux, on récupère des tourteaux qui contiennent encore une fraction importante des protéines et des phospholipides présents dans l'enveloppe des corps huileux. Ces tourteaux contiennent en outre un taux d'huile non extraite qui peut représenter de 10 à 30 % en poids.Furthermore, we know that during the extraction of oils oilseed plants, oilcakes are recovered which contain still a significant fraction of proteins and phospholipids present in the envelope of oily bodies. These cakes contain in addition to a rate of unextracted oil which can represent from 10 to 30% in weight.

La présente invention vise plus spécifiquement à fournir des compositions comprenant de nouvelles vésicules lipidiques et des émulsions les contenant, en valorisant les tourteaux d'oléagineux.The present invention more specifically aims to provide compositions comprising new lipid vesicles and emulsions containing them, enhancing oilseed meals.

A cet effet, la présente invention a pour objet des compositions cosmétiques, thérapeutiques ou alimentaires comprenant des vésicules lipidiques ayant une taille moyenne de 0,1 à 20 micromètres, notamment 1 à 8 micromètres, et comprenant une enveloppe constituée pratiquement de l'ensemble des protéines et des phospholipides présents dans les corps huileux des graines d'oléagineux, entourant un noyau comprenant au moins des lipides exogènes et/ou des substances lipophiles exogènes.To this end, the present invention relates to cosmetic, therapeutic or food compositions comprising lipid vesicles having an average size of 0.1 to 20 micrometers, in particular 1 to 8 micrometers, and comprising an envelope made up practically all of the proteins and phospholipids present in the oily bodies of oil seeds, surrounding a nucleus comprising at least exogenous lipids and / or lipophilic substances exogenous.

L'invention a également pour objet de telles compositions comprenant une émulsion aqueuse comprenant des vésicules lipidiques dispersées dans une phase aqueuse.The invention also relates to such compositions comprising an aqueous emulsion comprising lipid vesicles dispersed in an aqueous phase.

Dans la présente invention l'expression "pratiquement l'ensemble des protéines et des phospholipides présent dans les corps huileux des graines d'oléagineux" signifie que l'on retrouve dans l'enveloppe des vésicules pratiquement les mêmes constituants que dans l'enveloppe des corps huileux et que les protéines comprennent à la fois des protéines non glycosylées et des protéines glycosylées. En pratique, les protéines et les phospholipides présents dans les graines d'oléagineux sont ceux présents dans les tourteaux d'oléagineux.In the present invention the expression "practically all the proteins and phospholipids present in the body oily oilseeds "means that found in the envelope of the vesicles practically the same constituents as in the envelope of oily bodies and that proteins include both non-glycosylated proteins and glycosylated proteins. In practice, proteins and phospholipids found in oilseeds are those present in oilseed meals.

L'invention a également pour objet un procédé de fabrication d'une telle émulsion aqueuse, qui comprend :

  • le broyage de tourteaux d'oléagineux,
  • l'addition aux tourteaux broyés d'une phase lipidique de façon à avoir un pourcentage global de lipides de 50 à 95 % en poids,
  • le malaxage des tourteaux broyés et de la phase lipidique jusqu'à obtenir une pâte homogène, notamment à une température de 0 à 90° C,
  • l'addition d'une phase aqueuse à la pâte dans un rapport pondéral pâte/phase aqueuse d'environ 40/60 à 5/95, notamment à une température de 0 à 90° C,
  • l'agitation de la pâte et de la phase aqueuse pour former une émulsion,
  • et éventuellement la décantation et/ou la filtration de l'émulsion pour éliminer les particules solides,
  • et éventuellement la centrifugation de l'émulsion pour obtenir une émulsion concentrée.
The subject of the invention is also a process for manufacturing such an aqueous emulsion, which comprises:
  • grinding oilseed meals,
  • the addition to the ground cake of a lipid phase so as to have an overall percentage of lipids of 50 to 95% by weight,
  • kneading the ground cake and the lipid phase until a homogeneous paste is obtained, in particular at a temperature of 0 to 90 ° C.,
  • the addition of an aqueous phase to the dough in a dough / aqueous phase weight ratio of about 40/60 to 5/95, in particular at a temperature of 0 to 90 ° C,
  • stirring the dough and the aqueous phase to form an emulsion,
  • and optionally decantation and / or filtration of the emulsion to remove the solid particles,
  • and optionally centrifuging the emulsion to obtain a concentrated emulsion.

Comme exemples de tourteaux d'oléagineux, on peut citer les tourteaux de soja, pistache, macadamia, tournesol, colza, arachide, amande, noisette, sésame, bourrache, germe de blé, jojoba. On utilise de préférence des tourteaux obtenus à partir de graines à forte teneur en huile (pistache, macadamia, arachide, jojoba, noisette, amande).As examples of oilseed meals, we can cite soybean meal, pistachio, macadamia, sunflower, rapeseed, peanut, almond, hazelnut, sesame, borage, wheat germ, jojoba. We use preferably oil cakes obtained from seeds with a high oil content (pistachio, macadamia, peanut, jojoba, hazelnut, almond).

Le broyage des tourteaux peut être effectué par des broyeurs classiques, tels que des broyeurs à couteaux, avantageusement jusqu'à obtenir une taille de particules inférieure à 0,1 mm.The grinding of oil cakes can be carried out by conventional mills, such as knife mills, advantageously until a particle size of less than 0.1 mm is obtained.

Les tourteaux broyés peuvent être éventuellement soumis à une irradiation pour une débactérisation jusqu'à une intensité de 10 kgray et conservés sous atmosphère inerte en emballage hermétiquement clos.Ground cake may be subject irradiation for debacterization up to an intensity of 10 kgray and kept under inert atmosphere in hermetically sealed packaging.

Par lipides exogènes on désigne les lipides d'apport, c'est-à-dire que l'on ajoute et qui ne sont pas présents dans les tourteaux broyés. Ces lipides que l'on ajoute aux tourteaux broyés peuvent être des lipides du même type que ceux présents dans l'oléagineux utilisé (lipides endogènes) ou d'autres lipides. En général, il reste dans les tourteaux une proportion relativement importante de triglycérides et l'on ajoute des lipides de façon à avoir un pourcentage global de lipides de 50 à 95 % en poids.By exogenous lipids is meant the supply lipids, that is to say which are added and which are not present in the oil cakes crushed. These lipids which are added to the ground cakes can be lipids of the same type as those present in the oilseed used (lipids endogenous) or other lipids. In general, there remains a relatively large proportion of triglycerides and lipids are added so as to have an overall percentage of lipids of 50 to 95% by weight.

On règle la quantité de lipides en fonction de la taille des particules de l'émulsion finale que l'on veut obtenir. Ainsi, si l'on veut avoir des tailles de particules plus faibles, on diminue la quantité de lipides ajoutés.We adjust the amount of lipids according to the size of the particles of the final emulsion that we want to obtain. So if you want to have smaller particle sizes, the quantity of lipids is reduced added.

Outre ces lipides, on peut ajouter des substances lipophiles telles que des vitamines (vitamines D, A, E, K), des filtres solaires (tels que Parsol MCX et Parsol 1789 de Givaudan ou de la benzophénone-3), des mélanges lipophiles complexes (Titan M262CD de Kemira Oy) additionnés éventuellement d'huile minérale, de carotène, de silicone (par exemple DC 200 de Dow Corning), d'esters gras. In addition to these lipids, lipophilic substances can be added such as vitamins (vitamins D, A, E, K), sunscreens (such as Parsol MCX and Parsol 1789 from Givaudan or benzophenone-3), complex lipophilic mixtures (Titan M262CD from Kemira Oy) added possibly mineral oil, carotene, silicone (e.g. DC 200 from Dow Corning), fatty esters.

Le malaxage des tourteaux et de la phase lipidique ajoutée est alors effectué jusqu'à obtenir une pâte homogène. On opère avantageusement sous atmosphère non oxydante (sous vide ou sous azote).The mixing of the oil cake and the added lipid phase is then carried out until a homogeneous paste is obtained. We operate advantageously under a non-oxidizing atmosphere (under vacuum or under nitrogen).

Les vésicules lipidiques peuvent contenir de 0,01% à 100% en poids de lipides exogènes ou de substances lipophiles exogènes.Lipid vesicles can contain from 0.01% to 100% by weight of exogenous lipids or exogenous lipophilic substances.

La phase aqueuse est ensuite ajoutée, avantageusement à température ambiante et sous atmosphère inerte (sous vide ou sous azote). Cette phase aqueuse peut comprendre, outre de l'eau, différents constituants hydrophiles.The aqueous phase is then added, advantageously at room temperature and under an inert atmosphere (vacuum or nitrogen). This aqueous phase can comprise, in addition to water, various hydrophilic constituents.

L'addition de la phase aqueuse est généralement réalisée de façon à avoir un rapport pondéral pâte/phase aqueuse d'environ 40/60 à 5/95. On préfère un rapport 30/70 à 5/95.The addition of the aqueous phase is generally carried out so as to have a paste / aqueous phase weight ratio of about 40/60 at 5/95. We prefer a ratio 30/70 to 5/95.

Pour obtenir une émulsion, on soumet l'ensemble à une agitation qui peut être importante, à l'aide par exemple d'un broyeur colloïdal.To obtain an emulsion, the whole is subjected to a agitation which can be significant, for example using a grinder colloidal.

L'émulsion obtenue est alors soumise éventuellement à une décantation et/ou filtration, par exemple sur un tamis de 200 micromètres.The emulsion obtained is then optionally subjected to a decantation and / or filtration, for example on a sieve of 200 micrometers.

L'émulsion obtenue est relativement diluée et en général il est nécessaire de concentrer cette émulsion par centrifugation. A cet effet, on peut utiliser une centrifugeuse à assiettes adaptée au taux de la phase lipidique. Le produit obtenu est un concentrat de particules lipidiques dont le taux de composants lipophiles peut varier d'environ 20 à 70 % en poids suivant les conditions de fabrication.The emulsion obtained is relatively diluted and in general it it is necessary to concentrate this emulsion by centrifugation. To this end, you can use a plate centrifuge adapted to the phase rate lipid. The product obtained is a concentrate of lipid particles, the level of lipophilic components can vary from approximately 20 to 70% by weight according to the manufacturing conditions.

Avant ou après cette centrifugation, la suspension lipidique peut subir un traitement thermique dont les conditions peuvent varier de 2 secondes à 10 minutes pour des températures de 80° C à 140° C. On peut alors procéder, si désiré, à une opération d'homogénéisation à l'aide d'un appareil de type Gaulin par exemple, laquelle opération peut avoir des conditions de pression variant de 5 à 400.105 Pa.Before or after this centrifugation, the lipid suspension can undergo a heat treatment, the conditions of which can vary from 2 seconds to 10 minutes for temperatures from 80 ° C. to 140 ° C. An operation can then be carried out, if desired. homogenization using a Gaulin type device for example, which operation may have pressure conditions varying from 5 to 400.10 5 Pa.

Ce concentrat de particules lipidiques peut être repris et dilué avec une phase aqueuse du type décrit plus loin. Cette phase aqueuse peut être épaissie à l'aide de gélifiants tels que gomme xanthane, gomme sclerane, bentone et dérivés, cellulose et dérivés, carbopol et dérivés, caroube, carraghénanes et dérivés, présents à des concentrations de 0 à 2 % en poids.This concentrate of lipid particles can be taken up and diluted with an aqueous phase of the type described below. This phase aqueous can be thickened using gelling agents such as xanthan gum, sclerane gum, bentone and derivatives, cellulose and derivatives, carbopol and derivatives, carob, carrageenans and derivatives, present at concentrations from 0 to 2% by weight.

Le concentrat de particules lipidiques peut en outre être baratté suivant les techniques de laiteries pour obtenir un beurre que l'on comprime pour en exprimer l'eau.The concentrate of lipid particles can also be churned using dairy techniques to obtain a butter that is compresses to express the water.

Les émulsions ainsi obtenues ont en général des tailles moyennes de particules de 0,1 à 20 micromètres.The emulsions thus obtained generally have sizes particle sizes from 0.1 to 20 micrometers.

Les émulsions ainsi obtenues trouvent notamment des applications dans le domaine des produits cosmétiques et la présente invention a également pour objet des compositions cosmétiques comprenant des vésicules lipidiques selon l'invention (par exemple des compositions hydratantes, des compositions de protection solaire, des compositions nourrissantes).The emulsions thus obtained find in particular applications in the field of cosmetic products and the present a subject of the invention is also cosmetic compositions comprising lipid vesicles according to the invention (for example compositions moisturizers, sun protection compositions, compositions nourishing).

L'utilisation dans ces compositions d'un système émulsionnant naturel (oléosines, phospholipides) entraíne une meilleure tolérance cutanée du produit final.The use in these compositions of an emulsifying system natural (oleosins, phospholipids) leads to better tolerance the final product.

Dans le cas de préparation d'une émulsion à usage cosmétique, on peut par exemple utiliser une phase aqueuse comprenant:

  • Glycérine   5 à 10 %
  • Propylène glycol   5 à 10 %
  • Butane diol   5 à 10 %
  • Urée   1 à 5%
  • Sodium PCA   0,5 à 5 %
  • EDTA   0,05 à 0,1 %
  • Méthyl paraben   0,05 à 0,2 %
  • Propyl paraben   0,05 à 0,1 %
  • Butyl paraben   0,05 à 0,1 %
  • Ethanol   0,05 à 0,5 %
  • B H T   0,05 à 1 %
  • Alginate de sodium   1 à 5 %
  • Vitamine C et dérivés   0,05 à 1 %
  • Vitamine B et dérivés   0 à 1 %
  • Acide sorbique   0 à 1 %
  • Préparations aqueuses diverses d'oligo-éléments
  • Sulfite de sodium   0 à 0,4 %.
In the case of preparation of an emulsion for cosmetic use, it is possible, for example, to use an aqueous phase comprising:
  • Glycerin 5 to 10%
  • Propylene glycol 5 to 10%
  • Butane diol 5 to 10%
  • Urea 1 to 5%
  • Sodium PCA 0.5 to 5%
  • EDTA 0.05 to 0.1%
  • Methyl paraben 0.05 to 0.2%
  • Propyl paraben 0.05 to 0.1%
  • Butyl paraben 0.05 to 0.1%
  • Ethanol 0.05 to 0.5%
  • BHT 0.05 to 1%
  • Sodium alginate 1 to 5%
  • Vitamin C and derivatives 0.05 to 1%
  • Vitamin B and derivatives 0 to 1%
  • Sorbic acid 0 to 1%
  • Various aqueous preparations of trace elements
  • Sodium sulphite 0 to 0.4%.

Les émulsions selon l'invention trouvent également des applications dans le domaine des produits alimentaires. La présente invention a donc également pour objet des compositions alimentaires comprenant des vésicules lipidiques selon l'invention. Comme exemple on peut citer des suppléments lactés vitaminés sans cholestérol, des desserts lactés fermentés, des yaourts et des crèmes fouettées. Les desserts lactés fermentés et les yaourts peuvent être fabriqués par addition de souches de lactobacilles à une émulsion selon l'invention puis incubation 5 heures à 35° C environ. Les crèmes fouettées peuvent être obtenues par addition de 90 parties d'un propulseur (CO2 ou N2O) à 10 parties d'une émulsion concentrée selon l'invention, additionnée des additifs alimentaires habituels (arômes et sucres).The emulsions according to the invention also find applications in the field of food products. The present invention therefore also relates to food compositions comprising lipid vesicles according to the invention. As an example we can cite vitamin supplements without cholesterol, fermented milk desserts, yogurts and whipped creams. Fermented milk desserts and yogurts can be made by adding lactobacillus strains to an emulsion according to the invention and then incubating for 5 hours at approximately 35 ° C. Whipped creams can be obtained by adding 90 parts of a propellant (CO 2 or N 2 O) to 10 parts of a concentrated emulsion according to the invention, supplemented with the usual food additives (flavors and sugars).

Les émulsions selon l'invention trouvent également des applications dans le domaine des produits pharmaceutiques à usage humain ou vétérinaire, en liaison avec les qualités intrinsèques des oléosines (petite taille et lipophilie).The emulsions according to the invention also find pharmaceutical applications for use human or veterinary, in connection with the intrinsic qualities of oleosins (small size and lipophilicity).

La présente invention a ainsi également pour objet des compositions pharmaceutiques. Comme exemple on peut citer des compositions pour l'apport de vitamine E, de vitamines D ou d'hormones via des patchs transdermiques.The present invention thus also relates to pharmaceutical compositions. As an example we can cite compositions for the supply of vitamin E, vitamins D or hormones via transdermal patches.

En outre, il est à noter que les émulsions obtenues comprennent des protéines qui présentent une grande similitude avec les apolipoprotéines des mammifères; autrement dit, on pense que les lipases des mammifères reconnaissent les protéines des émulsions selon l'invention, ce qui permet la fixation des lipases sur les membranes des particules et par suite la dégradation des lipides substrats des lipases concernées.In addition, it should be noted that the emulsions obtained include proteins that are very similar to mammalian apolipoproteins; in other words, it is believed that lipases mammals recognize the proteins of the emulsions according to the invention, which allows the attachment of lipases on the membranes of the particles and consequently the degradation of the lipid substrates of the lipases concerned.

Les exemples suivants illustrent la présente invention.The following examples illustrate the present invention.

EXEMPLE 1EXAMPLE 1

On broie un tourteau d'arachide à l'aide d'un broyeur à couteaux jusqu'à obtenir une taille inférieure à 0,1 mm environ.We ground a peanut cake using a grinder knives until a size less than about 0.1 mm is obtained.

Le tourteau contient 20 % en poids environ de triglycérides.The meal contains approximately 20% by weight of triglycerides.

On ajoute à 50 parties de tourteau broyé 50 parties d'huile végétale (triglycérides d'arachide ou autre oléagineux). L'ensemble est malaxé sous vide à température ambiante jusqu'à obtenir une pâte homogène.50 parts of ground meal are added to 50 parts of oil vegetable (peanut or other oilseed triglycerides). The set is kneaded under vacuum at room temperature until a paste is obtained homogeneous.

On ajoute à cette pâte 900 parties d'eau. On soumet l'ensemble à température ambiante et sous vide à une vive agitation à l'aide d'un broyeur colloïdal réglé sur l'ouverture maximale.900 parts of water are added to this paste. We submit the whole at room temperature and under vacuum with vigorous stirring using a colloid mill set to the maximum opening.

On filtre sous tamis de 200 micromètres. On centrifuge éventuellement le filtrat qui est un lait très fluide dans une centrifugeuse de laiterie.Filtered under a 200 micrometer sieve. We centrifuge possibly the filtrate which is a very fluid milk in a centrifuge dairy.

On obtient un concentrat de particules lipidiques ayant une taille moyenne de 3 micromètres, contenant environ 60 % de triglycérides.A concentrate of lipid particles having a average size of 3 micrometers, containing approximately 60% of triglycerides.

EXEMPLE 2EXAMPLE 2

On opère comme à l'exemple 1 avec un tourteau de macadamia (contenant 25 % en poids de triglycérides), en ajoutant à 30 parties en poids de tourteaux, 70 parties en poids de triglycérides (huile de macadamia ou d'autres oléagineux).We operate as in Example 1 with a meal of macadamia (containing 25% by weight of triglycerides), adding to 30 parts by weight of meal, 70 parts by weight of triglycerides ( macadamia or other oilseeds).

L'eau est ajoutée à la pâte à raison de 900 parties en poids.Water is added to the dough at the rate of 900 parts by weight.

On obtient finalement un concentrat de particules lipidiques ayant une taille moyenne de 3 micromètres, ce concentrat contenant environ 60 % de triglycérides.Finally, a concentrate of lipid particles is obtained. having an average size of 3 micrometers, this concentrate containing about 60% of triglycerides.

On donnera ci-après des exemples de compositions obtenues selon le procédé de l'invention.Examples of compositions will be given below obtained according to the method of the invention.

Exemple A - Lait pour le visageExample A - Face milk

  • Eau   qs. 100 %Water qs. 100%
  • Gomme xanthane   1 à 2 %1-2% xanthan gum
  • Concentrat A   20 à 40 %Concentrate A 20 to 40%
  • Parfum   0,1 à 0,5 %Perfume 0.1 to 0.5%
  • Conservateurs   qs.Preservatives qs.

Le concentrat A est fabriqué comme décrit à l'exemple 1, à partir d'une huile végétale.Concentrate A is produced as described in Example 1, from vegetable oil.

Le pH varie de 5,5 à 6,5 (qs = acide citrique). Viscosité de 2000 à 3000 cP.The pH varies from 5.5 to 6.5 (qs = citric acid). Viscosity of 2000 to 3000 cP.

Exemple B - Lait solaire écran totalExample B - Total sunscreen milk

  • Eau   qs 100 %Water qs 100%
  • Gomme xanthane   1 à 2 %1-2% xanthan gum
  • Concentrat B   20 à 40 %Concentrate B 20 to 40%
  • Parfum   0,1 à 0,5 %Perfume 0.1 to 0.5%
  • Conservateurs   qs.Preservatives qs.

Le concentrat B est fabriqué comme décrit à l'exemple 1, à partir d'une huile composée par exemple de :

  • Triglycérides   qs 100 %
  • PARSOL 1789   1 à 5 %
  • PARSOL MCX   1 à 15 %
  • TITAN M262CD   1 à 10 %
Concentrate B is manufactured as described in Example 1, from an oil composed for example of:
  • Triglycerides qs 100%
  • PARSOL 1789 1 to 5%
  • PARSOL MCX 1 to 15%
  • TITAN M262CD 1 to 10%

Le pH varie de 5,5 à 6,5 (qs = acide citrique). Viscosité 2000 à 3000 cP.The pH varies from 5.5 to 6.5 (qs = citric acid). Viscosity 2000 to 3000 cP.

Exemple C - Lait hydratant pour le corpsExample C - Moisturizing Body Lotion

  • Eau   qs 100 %Water qs 100%
  • Glycérine   5 à 10 %Glycerin 5 to 10%
  • Gomme xanthane   1 à 2 %1-2% xanthan gum
  • Urée   1 à 5 %Urea 1 to 5%
  • Concentrat C   20 à 40 %Concentrate C 20 to 40%
  • Parfum   0,1 à 0,5 %Perfume 0.1 to 0.5%
  • Conservateurs   qsPreservatives qs

Le concentrat C est fabriqué comme décrit à l'exemple 1, à partir d'huile végétale additionnée d'esters gras du jojoba (5 à 10 %).Concentrate C is produced as described in Example 1, from vegetable oil with added fatty esters of jojoba (5 to 10%).

Le pH varie de 6,0 à 6,5 (qs = acide citrique), la viscosité de 2000 à 3000 cP.The pH varies from 6.0 to 6.5 (qs = citric acid), the viscosity from 2000 to 3000 cP.

Exemple D - Supplément lacté vitaminé sans cholestérolExample D - Cholesterol Free Vitamin Milk Supplement

  • Eau qs   100 %Water qs 100%
  • Vitamine C   1 %Vitamin C 1%
  • Gomme xanthane   0,5 à 1 %Xanthan gum 0.5 to 1%
  • Concentrat D   20 à 40 %Concentrate D 20 to 40%
  • Extrait de vanille   qsVanilla extract qs
  • Conservateurs   qsPreservatives qs

Le concentrat D est fabriqué comme décrit à l'exemple 1, à l'aide d'huile à forte teneur en triglycérides gamma linoléniques additionnée de vitamine D (500 Ul/g max) ou A (1500 Ul/g max). Concentrate D is produced as described in Example 1, using oil with high gamma linolenic triglyceride content added vitamin D (500 IU / g max) or A (1500 IU / g max).

Les conservateurs pourront être éliminés si les conditions suivantes sont adoptées :

  • débactérisation initiale du tourteau,
  • traitement UHT (120° C x 3 secondes) de la suspension, avant ou après les ajouts décrits,
  • conservation en Tétrapak ou équivalent, sinon, les conservateurs alimentaires seront choisis, et de préférence :
  • acide sorbique
  • parabens divers
  • sodium sulfite
  • BHT
le pH sera réglé à 6,5 ± 0,2 à l'aide d'acide citrique.Preservatives may be eliminated if the following conditions are adopted:
  • initial debacterization of the meal,
  • UHT treatment (120 ° C x 3 seconds) of the suspension, before or after the additions described,
  • conservation in Tétrapak or equivalent, otherwise, food preservatives will be chosen, and preferably:
  • sorbic acid
  • various parabens
  • sodium sulfite
  • BHT
the pH will be adjusted to 6.5 ± 0.2 using citric acid.

On donnera ci-après des résultats d'essais mettant en évidence les natures différentes des protéines présentes dans l'enveloppe des corps huileux.The results of the tests showing highlights the different natures of the proteins present in the envelope oily bodies.

EXEMPLE 3EXAMPLE 3

On a procédé comme à l'exemple 2 en partant d'un tourteau de macadamia.We proceeded as in Example 2, starting from an oil cake of macadamia.

A partir d'un concentrat de vésicules lipidiques, on a séparé les protéines par la méthode sur gradients d'urée après extraction des lipides à l'éther diéthylique (Millichip, Colloque Int. Lipides Végétaux).From a concentrate of lipid vesicles, we separated proteins by the urea gradient method after extraction of diethyl ether lipids (Millichip, Int. Plant Lipids Symposium).

Les protéines ont été remises en solution dans un tampon Tris/HCl 10 mM, SDS 0,07 M, pH 8.Proteins were redissolved in buffer Tris / HCl 10 mM, SDS 0.07 M, pH 8.

La purification des protéines a été réalisée par chromatographie de tamisage moléculaire sur colonne de Superose 6 équilibrée et éluée en tampon Tris/HCI 10 mM SDS 0,07 M, pH 8,2.Protein purification was carried out by chromatography molecular sieving on a balanced Superose 6 column and eluted in 10 mM Tris / HCl buffer 0.07 M SDS, pH 8.2.

On a séparé 50 fractions et testé les fractions 7, 36 et 43 correspondant à des pics d'élution. A cet effet on a utilisé une technique de type "dot-blot" avec un sérum dirigé contre la β-glucosidase du soja qui réagit avec les motifs glucidiques complexes communs à la plupart des plantes, qui contiennent des résidus α-1-3 glucose et β-1-2-xylose.We separated 50 fractions and tested fractions 7, 36 and 43 corresponding to elution peaks. For this purpose we used a technique of "dot-blot" type with a serum directed against soy β-glucosidase which reacts with complex carbohydrate patterns common to most plants, which contain α-1-3 glucose and β-1-2-xylose residues.

Les fractions 7 et 36 sont reconnues par le sérum dirigé contre la β-glucosidase, ce qui n'est pas le cas de la fraction 43. La reconnaissance est donc imputable à la présence de chaínes glycosidiques dans les fractions 7 et 36 qui n'apparaissent pas pour la fraction 43.Fractions 7 and 36 are recognized by the directed serum against β-glucosidase, which is not the case for fraction 43. The recognition is therefore due to the presence of glycosidic chains in fractions 7 and 36 which do not appear for fraction 43.

Claims (7)

  1. Cosmetic, therapeutic or nutritional composition comprising lipidic vesicles having a mean size of 0.1 to 20 micrometers and comprising an envelope formed essentially of the set of proteins and phospholipids present in the oily bodies of oleaginous seeds, surrounding a core comprising exogenous lipids and/or exogenous lipophilic substances.
  2. Composition according to claim 1, in which the proteins and the phospholipids of the said vesicles are those present in oil cakes.
  3. Composition according to claim 1 or claim 2, comprising an aqueous emulsion comprising the said lipidic vesicles dispersed in an aqueous phase.
  4. A method of making an aqueous emulsion for incorporation in a composition according to claim 3, comprising:
    grinding oil cakes,
    adding a lipidic phase to the ground cakes in such a manner as to obtain a total percentage of lipids from 50 to 95% by weight,
    kneading the ground cakes and the lipidic phase until a homogenous paste is obtained,
    adding an aqueous phase to the paste in ratio by weight of paste to aqueous phase of around 40/60 to 5/95,
    agitating the paste and the aqueous phase to form an emulsion,
    and optionally decanting and/or filtering the emulsion,
    and optionally centrifuging the emulsion to obtain a concentrated emulsion.
  5. A method according to claim 4, in which the addition of the aqueous phase and its mixing with the paste are effected at ambient temperature.
  6. A method according to claim 4 or claim 5, in which the addition of the aqueous phase and its mixing with the paste are effected under a non-oxidising atmosphere.
  7. A method according to any of claims 4 to 6, in which the concentrated emulsion is further churned.
EP95400967A 1994-05-02 1995-04-27 Cosmetical use of aqueous emulsions containing lipid vesicles Expired - Lifetime EP0680751B2 (en)

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Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5776536A (en) * 1996-12-23 1998-07-07 Igen, Inc. Reduced fat chocolate and method of manufacture
NZ501404A (en) * 1997-05-27 2001-09-28 Sembiosys Genetics Inc Emulsion preparation comprising washed oil bodies of uniform size, shape and density
US6599513B2 (en) 1997-05-27 2003-07-29 Sembiosys Genetics Inc. Products for topical applications comprising oil bodies
US6761914B2 (en) 1997-05-27 2004-07-13 Sembiosys Genetics Inc. Immunogenic formulations comprising oil bodies
US7585645B2 (en) * 1997-05-27 2009-09-08 Sembiosys Genetics Inc. Thioredoxin and thioredoxin reductase containing oil body based products
US6372234B1 (en) 1997-05-27 2002-04-16 Sembiosys Genetics Inc. Products for topical applications comprising oil bodies
EP1905309A1 (en) * 1997-05-27 2008-04-02 SemBioSys Genetics Inc. Uses of oil bodies
AU772919C (en) * 1997-05-27 2004-12-16 Sembiosys Genetics Inc. Uses of oil bodies
US20050106157A1 (en) * 1997-05-27 2005-05-19 Deckers Harm M. Immunogenic formulations comprising oil bodies
CN1054965C (en) * 1997-08-18 2000-08-02 苏望懿 Method for prodn. of phospholipid by using hydrated oil foot
EP1131047A1 (en) * 1998-11-25 2001-09-12 SemBioSys Genetics, Inc. Oil bodies as topical delivery vehicles for active agents
ATE485385T1 (en) * 2000-01-19 2010-11-15 Martek Biosciences Corp SOLVENT-FREE EXTRACTION PROCESS
US6395690B1 (en) * 2001-02-28 2002-05-28 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Process for making mild moisturizing liquids containing large oil droplet
WO2007122422A2 (en) * 2006-04-13 2007-11-01 The Boots Company Plc Composition and uses thereof
WO2007122421A2 (en) * 2006-04-13 2007-11-01 The Boots Company Plc Composition and uses thereof
EP1952695A1 (en) * 2007-01-31 2008-08-06 Unilever N.V. Oil bodies and method of producing such oil bodies
IT1392901B1 (en) * 2008-07-23 2012-04-02 Giuliani Spa MODIFIED OILS AND MULTIPLE EMULSIONS
EP2228052A1 (en) * 2009-03-09 2010-09-15 Coty Deutschland GmbH Cosmetic basic composition and use thereof
ES2758782T3 (en) 2010-06-01 2020-05-06 Dsm Ip Assets Bv Extraction of lipid from cells and products thereof
US20140220217A1 (en) 2011-07-12 2014-08-07 Maraxi, Inc. Method and compositions for consumables
RU2653751C2 (en) 2011-07-12 2018-05-14 Импоссибл Фудз Инк Methods and compositions for consumables
CN103796530A (en) 2011-07-12 2014-05-14 马拉克西公司 Methods and compositions for consumables
WO2014110539A1 (en) 2013-01-11 2014-07-17 Maraxi, Inc. Methods and compositions for consumables
US10039306B2 (en) 2012-03-16 2018-08-07 Impossible Foods Inc. Methods and compositions for consumables
CN102894109B (en) * 2012-10-12 2015-04-15 山东天博食品配料有限公司 Method for preparing composite flavor oil powder grease
EP2943077B1 (en) 2013-01-11 2018-10-31 Impossible Foods Inc. Non-dairy ricotta cheese replica
SG11201605043TA (en) 2013-12-20 2016-07-28 Dsm Ip Assets Bv Processes for obtaining microbial oil from microbial cells
NZ721413A (en) 2013-12-20 2022-05-27 Dsm Ip Assets Bv Processes for obtaining microbial oil from microbial cells
MX370606B (en) 2013-12-20 2019-12-18 Dsm Ip Assets Bv Processes for obtaining microbial oil from microbial cells.
AU2015240911B2 (en) 2014-03-31 2018-11-08 Impossible Foods Inc. Ground meat replicas
EP3362151B1 (en) 2015-10-15 2020-08-05 Cargill, Incorporated Composition containing oleosomes of different size distribution
FR3072288A1 (en) * 2017-10-16 2019-04-19 Isabelle Desjardins-Lavisse OIL-IN-WATER EMULSION BASED ON VEGETABLE OILS AND FORMULATED WITHOUT SURFACTANTS

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3346390A (en) * 1963-12-06 1967-10-10 Swift & Co Process for preparing nut butter from soybeans
US3619207A (en) * 1969-08-14 1971-11-09 Procter & Gamble Peanut butter containing homogenized peanut paste
US3995068A (en) * 1972-11-21 1976-11-30 Gerber Products Company Method of making sweetened storage stable peanut butter spread and product thereof
US3903311A (en) * 1972-11-21 1975-09-02 Gerber Prod Sweetened storage stable peanut butter spread
US4078361A (en) * 1976-11-15 1978-03-14 Hartness Thomas P Apparatus for controlling the flow of articles to a case packer
US4088795A (en) † 1976-11-19 1978-05-09 Mead Johnson & Company Low carbohydrate oilseed lipid-protein comestible
US4324802A (en) † 1979-12-18 1982-04-13 L'oreal Cosmetic oil and composition containing the same
FR2509988B1 (en) † 1981-07-23 1986-05-30 Oreal MIXTURE OF VEGETABLE OILS BASED ON JOJOBA OIL AS AN OXIDATION STABILIZING AGENT AND COSMETIC COMPOSITIONS CONTAINING THE SAME
JPS6158539A (en) * 1984-08-29 1986-03-25 Nisshin Oil Mills Ltd:The Preparation of snack-like cake
LU86021A1 (en) † 1985-07-24 1987-02-04 Oreal USE OF LUPINE SEED POWDER IN THE PRODUCTION OF COSMETIC OR DERMOPHARMACEUTICAL COMPOSITIONS AND COMPOSITIONS THUS OBTAINED
US4847106A (en) * 1985-09-30 1989-07-11 Rme Research Associates Method of pressing sesame seeds
US4650857A (en) * 1985-12-18 1987-03-17 Morse Capital Corporation Bland protein concentrates from peanuts and process for making
US4810498A (en) † 1986-02-13 1989-03-07 The Peau Corporation Nail oil composition
US4701471A (en) † 1986-04-16 1987-10-20 Loucks Sr Joseph Skin care composition
US5306513A (en) * 1986-10-24 1994-04-26 Joyce Colucci Cones formed from roll dough
US4942055A (en) * 1986-12-18 1990-07-17 Pbfb Licensing Corporation Gravitationally-stabilized peanut-containing composition
FR2618332B1 (en) † 1987-07-23 1990-04-27 Synthelabo LIPID EMULSION FOR PARENTERAL OR ENTERAL NUTRITION
FR2657256B1 (en) * 1990-01-24 1994-09-16 Claude Bonne NEW COSMETIC PREPARATIONS CONTAINING AN EXTRACT OF SUNFLOWER MEAL (HELIANTHUS ANNUUS).
US5230919A (en) * 1991-05-10 1993-07-27 The Procter & Gamble Company Composition and process of making fluid, reduced fat peanut butters and improved whipped peanut butters
US5240734A (en) * 1991-05-31 1993-08-31 Healthy Foods Solutions Reduced-fat peanut butter compositions and methods for preparing same
US5225230A (en) * 1991-09-17 1993-07-06 West Central Cooperative Method for preparing a high bypass protein product
US5436023A (en) * 1994-04-29 1995-07-25 Pbfb Licensing Corporation Process for roasting food slurries

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DE69518455T2 (en) 2001-01-04
KR100220554B1 (en) 1999-09-15
KR950031016A (en) 1995-12-18
JPH0840877A (en) 1996-02-13
DE69518455D1 (en) 2000-09-28
BR9501877A (en) 1995-11-28
EP0680751B2 (en) 2004-11-24
ATE195651T1 (en) 2000-09-15
CN1116903A (en) 1996-02-21
CA2148311C (en) 1999-12-21
FR2719222B1 (en) 1996-06-21
DE69518455T3 (en) 2005-08-18
FR2719222A1 (en) 1995-11-03
JP2826081B2 (en) 1998-11-18
EP0680751A1 (en) 1995-11-08
CA2148311A1 (en) 1995-11-03
US5683740A (en) 1997-11-04

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